I [M] had an unexpected night with my sister’s best friend [F]

Well after lurking for a long time, I finally have a story of my own! Alt acct. And name changes For obvious reasons. Also, I’m on mobile so apologies for formatting issues.

A little back story. I’ve been trying to end things with my gf for a little while but she’s been stubborn and I’m too concerned about her well being too break her heart enough to accept a breakup. Along with this, my sister’s best friend Jenna had been flirty with me for a few years. I recently moved back in with my parents until I get a new place because I got a new job, and I’ve been seeing Jenna a lot more often.

Jenna is cute, about 5’4″ with big eyes, fairly small chested, light brown hair, and super friendly. I’ve always found her rather attractive, despite her not being my usual type. I always had fun being flirty with her. I guess it was the confidence boost, because I’ve had no intention of cheating on my gf regardless of our situation.

That has been the case until last night. After several drinks shared among me, my sister, and Jenna, the conversations were all over the place. Eventually my sister decided she wanted to take a walk to the gas station to pick up some more beer, but Jenna and I were happy with the ipa’s we had in the fridge.

So my sister leaves us alone while we watch some crappy thing on Netflix and chat. We were goofing off and Jenna threw a pillow at my face, so I guilted her into giving me a kiss on the cheek. Thinking I’m sly af, I turned my head so she planted the kiss right on my lips. She pulled away promptly, but I could feel a very slight buzz of electricity between us. A little bit later, my drunk ass mentioned I wanted to try it again. “Try what?” Jenna said. I moved in for another kiss, only to find her lips pressed tight.

I knew I had gone too far this time. I apologized and she mentioned my girlfriend and her boyfriend. The boyfriend was news to me, but I respect it. While waiting for my sister, we kept talking about everything that came to mind. I was morbidly curious about this boyfriend of hers (considering the months of flirting up to this point), and I learned that Jenna was in a similar situation where she can’t break up with this dude for many reasons. Some I found silly, but others I really understood. A while later we still hadn’t heard from my sister so Jenna called her. My starter had gone to her room and fell asleep taking to her latest dude.

Giving up on my sister rejoining us, Jenna and I kept talking and drinking. Conversation bounced from topic to topic until I finally had enough nerve and alcohol in me that I told her I wanted to try the kiss again. She confessed that she had wanted to kiss back, but she had several reservations. We kept talking about it when, seemingly all of a sudden, she reached her head up for a kiss.

I wasted no time. We kissed gently, just feeling each other out for a while. It didn’t take long to morph into a full make-out session, complete with all the heavy petting a jr. high kid would kill for. The more we kissed and felt each other, the more intense it got. I reached down between her legs and rubbed through her pants. “Careful, you’re making me horny,” she said, which only served to make me want to go further. We kept going. I couldn’t get enough of her small breasts. They were firm, a perfect handful size, and her nipples were beautifully hard.

After a few more minutes, she got up, grabbed my hand, and led me to my bedroom. She laid down on my bed, and I came down on top of her, kissing her wonderful lips, her neck, nibbling her ear (which she thoroughly enjoyed), and feeling her all over. I lifted her shirt up over her boobs and kissed my way down. I kissed between her perfect little breasts, and kissed my way to her nipples to suck on them playfully. As I was doing this, I worked her pants over her hips. “No underwear,” she said to my delight, “I hate underwear.”

I kissed my way down, I kissed and gently bit her stomach, her legs, her hips, everything I could to increase the tension before I started eating her out. She’s not incredibly vocal, but she made it clear she was enjoying it. I could tell just with my tongue that she was much tighter than I expected, so I wetted a finger and slid it in, only to recieve more sounds of approval. This went on for a while. I was too drunk to know how long, but eventually she told me she wanted to feel me inside her.

I pulled my pants off, held her knees to either side of her chest, and guided myself in. I don’t claim to have a huge schlong, but I’m rather proud of it. I was also about as hard as an anatomy midterm since I’d been without an interaction like this for a few months by then.

I went slow, I went fast, I angled myself to hit her g-spot, I went as deep as I could go. The last one got the biggest response from her, so much so that I thought she was in pain, since I definitely bottomed out in her small pussy. She told me she liked it and I kept going. I mixed it up as much as I could, but don’t forget, I’m 8 beers deep. There’s no way I could get particularly creative. After a little while I asked her to get on top.

Boy oh boy was I unready for that treat. I got to watch her beautiful future, feel her making herself feel good, and I got to play to my hearts content. It was truly incredible. I can’t remember the last time I was so smitten my a gorgeous set of boobs.

We slowed down a bit after we came to terms with the fact that we were both too drunk to have an orgasm. Finally I asked one more thing of her. I wanted to eat her out again, make her feel good and taste her again. She swung a leg over my face and went to town sucking my dick while I licked and sucked her. I was even able to stick a spit -lubed finger in her even tighter asshole, to which she responded with some rather wonderful noises.

After a little while longer, she got up to go get more water while I waited patiently for her to return.

When she did, I got her onto her back and when in missionary style once again. We just kept going, enjoying how each other felt, complimenting each other, and damn did I love the way she smelled.

By then the sun had come up. It was 5am, and my sister would be up soon. Jenna kissed me again, long and deep, after we put our clothes back on. Then she went out the door, got in her car, and went home.

It’s now 8am that very morning. I won’t be able to get this off my mind for quite some time.

Source: reddit.com/r/gonewildstories/comments/cd46gw/i_m_had_an_unexpected_night_with_my_sisters_best